organic chemistry Organic chemistry is a subdiscipline within chemistry involving the scientific study of the structure, properties, and reactions of organic compounds and organic materials, i.e., matter in its various forms that contain carbon atoms.Clayden, J.; ...

, a vinyl group (abbr. Vi;

IUPAC name In chemical nomenclature, a preferred IUPAC name (PIN) is a unique name, assigned to a chemical substance and preferred among the possible names generated by IUPAC nomenclature. The "preferred IUPAC nomenclature" provides a set of rules for cho ...

: ethenyl group) is a

functional group In organic chemistry, a functional group is a substituent or moiety in a molecule that causes the molecule's characteristic chemical reactions. The same functional group will undergo the same or similar chemical reactions regardless of the rest ...

with the formula . It is the

ethylene Ethylene (IUPAC name: ethene) is a hydrocarbon which has the formula or . It is a colourless, flammable gas with a faint "sweet and musky" odour when pure. It is the simplest alkene (a hydrocarbon with carbon-carbon double bonds). Ethylene i ...

(IUPAC name: ethene) molecule () with one fewer

hydrogen Hydrogen is the chemical element with the symbol H and atomic number 1. Hydrogen is the lightest element. At standard conditions hydrogen is a gas of diatomic molecules having the formula . It is colorless, odorless, tasteless, non-toxic, an ...

atom. The name is also used for any compound containing that group, namely where R is any other group of atoms. An industrially important example is

vinyl chloride Vinyl chloride is an organochloride with the formula H2C=CHCl. It is also called vinyl chloride monomer (VCM) or chloroethene. This colorless compound is an important industrial chemical chiefly used to produce the polymer polyvinyl chloride (PVC ...

, precursor to PVC, a plastic commonly known as ''vinyl''. Rollup chessboard

Vinyl is one of the

alkenyl In organic chemistry, an alkene is a hydrocarbon containing a carbon–carbon double bond. Alkene is often used as synonym of olefin, that is, any hydrocarbon containing one or more double bonds.H. Stephen Stoker (2015): General, Organic, a ...

functional groups. On a carbon skeleton, sp²-hybridized carbons or positions are often called vinylic.

Allyl In organic chemistry, an allyl group is a substituent with the structural formula , where R is the rest of the molecule. It consists of a methylene bridge () attached to a vinyl group (). The name is derived from the scientific name for garlic, ...

acrylate Acrylates (IUPAC: prop-2-enoates) are the salts, esters, and conjugate bases of acrylic acid. The acrylate ion is the anion C H2=CHC OO−. Often, acrylate refers to esters of acrylic acid, the most common member being methyl acrylate. These acr ...

s and styrenics contain vinyl groups. (A styrenic crosslinker with two vinyl groups is called '' divinyl benzene''.)

Vinyl polymers

Vinyl groups can

polymerize In polymer chemistry, polymerization (American English), or polymerisation (British English), is a process of reacting monomer molecules together in a chemical reaction to form polymer chains or three-dimensional networks. There are many for ...

with the aid of a radical initiator or a catalyst, forming

vinyl polymer In polymer chemistry, vinyl polymers are a group of polymers derived from substituted vinyl () monomers. Their backbone is an extended alkane chain . In popular usage, "vinyl" refers only to polyvinyl chloride (PVC). Examples Vinyl polymers are ...

s. Vinyl polymers contain no vinyl groups. Instead they are saturated. The following table gives some examples of vinyl polymers.

Reactivity

Vinyl derivatives are

alkene In organic chemistry, an alkene is a hydrocarbon containing a carbon–carbon double bond. Alkene is often used as synonym of olefin, that is, any hydrocarbon containing one or more double bonds.H. Stephen Stoker (2015): General, Organic, an ...

s. If activated by an adjacent group, the increased polarization of the bond gives rise to characteristic reactivity, which is termed

vinylogous In organic chemistry, vinylogy is the transmission of electronic effects through a conjugated organic bonding system. The concept was introduced in 1926 by Ludwig Claisen to explain the acidic properties of formylacetone and related ketoaldehydes ...

: * In

allyl In organic chemistry, an allyl group is a substituent with the structural formula , where R is the rest of the molecule. It consists of a methylene bridge () attached to a vinyl group (). The name is derived from the scientific name for garlic, ...

compounds, where the next carbon is saturated but substituted once,

allylic rearrangement An allylic rearrangement or allylic shift is an organic reaction in which the double bond in an allyl chemical compound shifts to the next carbon atom. It is encountered in nucleophilic substitution. In reaction conditions that favor a SN1 react ...

and related reactions are observed. ** Allyl

Grignard reagent A Grignard reagent or Grignard compound is a chemical compound with the general formula , where X is a halogen and R is an organic group, normally an alkyl or aryl. Two typical examples are methylmagnesium chloride and phenylmagnesium bromide ...

s (organomagnesiums) can attack with the vinyl end first. * If next to an electron-withdrawing group,

conjugate addition Nucleophilic conjugate addition is a type of organic reaction. Ordinary nucleophilic additions or 1,2-nucleophilic additions deal mostly with additions to carbonyl compounds. Simple alkene compounds do not show 1,2 reactivity due to lack of polarit ...

(Michael addition) can occur. Vinyl organometallics, e.g.

vinyllithium Vinyllithium is an organolithium compound with the formula LiC2H3. A colorless or white solid, it is encountered mainly as a solution in tetrahydrofuran (THF). It is a reagent in synthesis of organic compounds.. Preparation and structure So ...

and

vinyl tributyltin Vinyl tributyltin is an organotin compound with the formula Bu3SnCH=CH2 (Bu = butyl). It is a white, air-stable solid. It is used as a source of vinyl anion equivalent in Stille coupling reactions. As a source of vinyltin reagents, early work u ...

, participate in coupling reactions such as in

Negishi coupling The Negishi coupling is a widely employed transition metal catalyzed cross-coupling reaction. The reaction couples organic halides or triflates with organozinc compounds, forming carbon-carbon bonds (C-C) in the process. A palladium (0) specie ...

Etymology

The

etymology Etymology ()The New Oxford Dictionary of English (1998) – p. 633 "Etymology /ˌɛtɪˈmɒlədʒi/ the study of the class in words and the way their meanings have changed throughout time". is the study of the history of the Phonological chan ...

of ''vinyl'' is the

Latin Latin (, or , ) is a classical language belonging to the Italic branch of the Indo-European languages. Latin was originally a dialect spoken in the lower Tiber area (then known as Latium) around present-day Rome, but through the power of the ...

''vinum'' = "

wine Wine is an alcoholic drink typically made from fermented grapes. Yeast consumes the sugar in the grapes and converts it to ethanol and carbon dioxide, releasing heat in the process. Different varieties of grapes and strains of yeasts are m ...

", and the

Greek Greek may refer to: Greece Anything of, from, or related to Greece, a country in Southern Europe: *Greeks, an ethnic group. *Greek language, a branch of the Indo-European language family. **Proto-Greek language, the assumed last common ancestor ...

word "hylos" 'υλος (matter or material), because of its relationship with

ethyl alcohol Ethanol (abbr. EtOH; also called ethyl alcohol, grain alcohol, drinking alcohol, or simply alcohol) is an organic compound. It is an alcohol with the chemical formula . Its formula can be also written as or (an ethyl group linked to a hyd ...

. The term "vinyl" was coined by the German chemist

Hermann Kolbe Adolph Wilhelm Hermann Kolbe (27 September 1818 – 25 November 1884) was a major contributor to the birth of modern organic chemistry. He was a professor at Marburg and Leipzig. Kolbe was the first to apply the term synthesis in a chemical cont ...

in 1851.H. Kolbe (1851)
"On the chemical constitution and nature of organic radicals,"
''The Quarterly Journal of the Chemical Society of London'', 3 (4) : 369-405; see footnote o
page 376.
/ref>

References

{{Functional group Alkenyl groups Monomers Functional groups

Vinyl polymers

Reactivity

Etymology

See also

References